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Microluside A

Family: Monera - Micrococcaceae
Kingdom: Monera
Class: Xanthone

Canonical Smiles	OC[C@H]1OC(Oc2cccc3c2oc2c(cccc2c3=O)OC2O[C@H](CO)[C@H]([C@@H]([C@H]2OC(=O)c2ccc(cc2)O)O)O)[C@@H]([C@H]([C@@H]1OC1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)OC(=O)c1ccc(cc1)O)O)O
InChI	InChI=1S/C45H46O23/c46-15-26-30(52)31(53)40(67-42(59)19-9-13-21(50)14-10-19)45(62-26)61-25-6-2-4-23-29(51)22-3-1-5-24(36(22)65-37(23)25)60-43-34(56)33(55)39(28(17-48)63-43)68-44-35(57)32(54)38(27(16-47)64-44)66-41(58)18-7-11-20(49)12-8-18/h1-14,26-28,30-35,38-40,43-50,52-57H,15-17H2/t26-,27-,28-,30-,31+,32-,33-,34-,35-,38-,39-,40-,43?,44?,45?/m1/s1
InChIKey	BGZRIXRLEGZUKI-FXANPTARSA-N
Formula	C₄₅H₄₆O₂₃
HBA	23
HBD	11
MW	954.84
Rotatable Bonds	13
TPSA	360.72
LogP	-1.73
Number Rings	8
Number Aromatic Rings	5
Heavy Atom Count	68
Formal Charge	0
Fraction CSP3	0.4
Exact Mass	954.24
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Micrococcus species EG45	Micrococcaceae	Monera	1269

Showing of synonyms

Eltamany EE, Abdelmohsen UR, et al. (2014). New antibacterial xanthone from the marine sponge-derived Micrococcus sp. EG45. Bioorganic and Medicinal Chemistry Letters,2014,24(21),4939-4942. [View] [PubMed]

Pubchem: 163062997

No compound-protein relationship available.

SMILES: c1ccccc1C(=O)OC2C(OCCC2)Oc(ccc3)c(c34)oc5c(c4=O)cccc5OC(OC6)CCC6OC(OC7)CCC7OC(=O)c8ccccc8

Level: 5

Mol. Weight: 954.84 g/mol

SMILES: c1ccccc1C(=O)OC2CCC(OC2)OC3CCC(OC3)Oc(ccc4)c(c45)oc6c(c5=O)cccc6OC7CCCCO7

Level: 4

Mol. Weight: 954.84 g/mol

SMILES: c1ccccc1C(=O)OC2C(OCCC2)Oc(ccc3)c(c34)oc5c(c4=O)cccc5OC(OC6)CCC6OC7CCCCO7

Level: 4

Mol. Weight: 954.84 g/mol

SMILES: c1ccccc1C(=O)OC2CCC(OC2)OC3CCC(OC3)Oc(ccc4)c(c45)oc6c(c5=O)cccc6

Level: 3

Mol. Weight: 954.84 g/mol

SMILES: c1ccccc1C(=O)OC2C(OCCC2)Oc(ccc3)c(c34)oc5c(c4=O)cccc5OC6CCCCO6

Level: 3

Mol. Weight: 954.84 g/mol

SMILES: O1CCCCC1OC2CCC(OC2)Oc(ccc3)c(c34)oc5c(c4=O)cccc5OC6CCCCO6

Level: 3

Mol. Weight: 954.84 g/mol

SMILES: c1ccccc1C(=O)OC2C(OCCC2)Oc(ccc3)c(c34)oc5c(c4=O)cccc5

Level: 2

Mol. Weight: 954.84 g/mol

SMILES: c1cccc(c2=O)c1oc(c23)c(ccc3)OC(OC4)CCC4OC5CCCCO5

Level: 2

Mol. Weight: 954.84 g/mol

SMILES: O1CCCCC1Oc(ccc2)c(c23)oc4c(c3=O)cccc4OC5CCCCO5

Level: 2

Mol. Weight: 954.84 g/mol

SMILES: c1ccccc1C(=O)OC2CCC(OC2)OC3CCCOC3

Level: 2

Mol. Weight: 954.84 g/mol

SMILES: c1cccc(c2=O)c1oc(c23)c(ccc3)OC4CCCCO4

Level: 1

Mol. Weight: 954.84 g/mol

SMILES: c1ccccc1C(=O)OC2CCCOC2

Level: 1

Mol. Weight: 954.84 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 954.84 g/mol

SMILES: c1cccc(c12)oc3c(c2=O)cccc3

Level: 0

Mol. Weight: 954.84 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 954.84 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 954.84 g/mol

Antimicrobial

Absorption

Caco-2 (logPapp): -6.3
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 20661.69
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 2701051.04

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.57
Plasma Protein Binding: 44.46
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Non-Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Inhibitor

Excretion

Clearance: 4.33
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Toxic
Bee: Safe
Bioconcentration Factor: -62815.47
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.06
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.05
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -4902275744.69
Rat (Acute): 2.82
Rat (Chronic Oral): 13.32
Fathead Minnow: 6188089.82
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 551362572.07
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -292.18
Log(P): 0.68
Log S: -4.41
Log(Vapor Pressure): -18156004.51
Melting Point: 248.01
pKa Acid: -132225.91
pKa Basic: -1053.53

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9301
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9301
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.8953
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.8953
Protease	O38896	O38896_9HIV1	Human immunodeficiency virus 1	3	0.8900
Protease	O38896	O38896_9HIV1	Human immunodeficiency virus 1	3	0.8900
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.8633
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.8633
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8247
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8247
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.8177
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.8177
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.8155
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.8155
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.8116
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.8116
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7963
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7963
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	3	0.7922
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	3	0.7922
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.7831
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.7831
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7768
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7768
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.7701
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.7701
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7575
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7575
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7504
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7504
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7495
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7495
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7488
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7488
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7474
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7474
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7460
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7460
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7445
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7445
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7435
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7435
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7400
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7400
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7371
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7371
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7370
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7370
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7359
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7359
CCR4-NOT transcription complex subunit 6-like	Q96LI5	CNO6L_HUMAN	Homo sapiens	4	0.7330
CCR4-NOT transcription complex subunit 6-like	Q96LI5	CNO6L_HUMAN	Homo sapiens	4	0.7330
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7320
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7320
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7311
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7311
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.7310
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.7310
Beta sliding clamp	P0A988	DPO3B_ECOLI	Escherichia coli	3	0.7294
Beta sliding clamp	P0A988	DPO3B_ECOLI	Escherichia coli	3	0.7294
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7292
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7292
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7251
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7251
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7214
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7214
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7175
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7175
Phosphoglycerate kinase	Q83AU6	PGK_COXBU	Coxiella burnetii	3	0.7144
Phosphoglycerate kinase	Q83AU6	PGK_COXBU	Coxiella burnetii	3	0.7144
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7135
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7135
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7132
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7132
7-methylguanosine phosphate-specific 5'-nucleotidase	Q9W197	5NT3B_DROME	Drosophila melanogaster	4	0.7083
7-methylguanosine phosphate-specific 5'-nucleotidase	Q9W197	5NT3B_DROME	Drosophila melanogaster	4	0.7083
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7040
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7040
Ethylene receptor 1	P49333	ETR1_ARATH	Arabidopsis thaliana	3	0.7035
Ethylene receptor 1	P49333	ETR1_ARATH	Arabidopsis thaliana	3	0.7035
Adenosine 5'-monophosphoramidase HINT1	P80912	HINT1_RABIT	Oryctolagus cuniculus	3	0.7018
Adenosine 5'-monophosphoramidase HINT1	P80912	HINT1_RABIT	Oryctolagus cuniculus	3	0.7018
Threonine--tRNA ligase	P0A8M3	SYT_ECOLI	Escherichia coli	3	0.7014
Virulence sensor histidine kinase PhoQ	P0DM80	PHOQ_SALTY	Salmonella typhimurium	3	0.7014
Virulence sensor histidine kinase PhoQ	P0DM80	PHOQ_SALTY	Salmonella typhimurium	3	0.7014
Threonine--tRNA ligase	P0A8M3	SYT_ECOLI	Escherichia coli	3	0.7014
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7011
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7011

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